The Windy Pines, My Third Summer - Cover

The Windy Pines, My Third Summer

Copyright© 2022 by Fanlon

Chapter 26

Coming of Age Sex Story: Chapter 26 - Another year, another summer at The Windy Pines. Sam gets to explore more of his relationship with Mary, as well as Sara and a couple others. The biggest question though is, do the rules get broken. You're going to have to read and find out! This is the third installment of the award-winning series The Windy Pines.

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   mt/Fa   ft/ft   Fa/ft   Mult   Teenagers   Incest   Mother   Brother   Sister   Cousins   Group Sex   Exhibitionism   Masturbation   Voyeurism   Public Sex   Nudism  

I managed two more rounds before I eventually passed out with my arms around Sara as she spooned up in front of me. After Amy’s blowjob, Amy and I didn’t touch each other again the rest of the night, not on purpose anyway. Mary recovered and participated for the last hour or so. She had no idea what Amy had done though. I didn’t say anything and neither did Sara or Amy. I knew when she found out though, there could be hell to pay.

The next morning was a somber affair. We were all slow to wake up. It’s as if we all had the same idea that if we didn’t wake up, then it wasn’t time for Amy and Mary to go home. Thankfully, Mary didn’t throw another fit about having to go. She had come to terms with it and after last night’s goodbye foursome, so she didn’t have a lot to complain about. Well, nothing that she knew about.

Once we did wake up, there were some moans and groans of complaint. Mary and Amy didn’t dawdle too long getting their things together and loading it all in Amy’s car. By lunch, we were sharing hugs and saying our goodbyes. I had thought about trying to get a last second quickie in, but I thought better of it. If I opened that can of worms, there was no telling when they would have finally got on the road and the last thing I needed was Mary’s parents being upset with me for making them get a late start.

Mom and Dad came over to give the girls each a hug as well before loading them in the car and we all watched as they drove away. It sucked because they were leaving. That didn’t mean there weren’t things to still be excited about for Sara and me. We had the cabin all to ourselves now. There was no limit to the things we could get into. Mom knew it too, because she gave me a sideways look when Sara said we should go inside and figure out what we were going to do for supper.

For the last few weeks of our summer at The Windy Pines, Sara and I did everything together, just the two of us. If I am honest, I loved those few weeks more than I even knew at the time. Every morning I still spent my morning drinking coffee and then masturbating with Mom on our parents’ porch swing. Those mornings were different though. Not that we did anything different, we didn’t, but there was a definite change in the look on Mom’s face, the way she watched and how her eyes seemed to see more than what was really there. Maybe she didn’t see more, but something was going on in her eyes.

We did get closer to each other as the days went by. Usually, I was on one side of the swing, and she was on the other. It was like we were afraid to be too close because we might do something we couldn’t undo and start something we couldn’t finish. Mom and I never said anything about the tension that was building. I’m not sure if that was a good thing, but I didn’t want what we had to end then or in the future. I was sure there was one time Mom’s hand started to move towards me, but she quickly pulled it back when I noticed. I don’t know if she meant to do it, but it happened.

Sara and I would spend most of our time at the hot spring or the pool area. If we weren’t there, we were usually at the cabin making love. Without Amy or Mary there, we took our time when we had sex. Sure, we were excited and urgent, but we didn’t have any real reason to be in a rush. Two and sometimes three times a day we would have sex. On rare occasion we would fuck. Those times it was just about racing to our orgasms, the heat of the moment spurring us on. In the evenings we would have supper with Mom and Dad if we didn’t want to cook, which was almost every night. I was a terrible cook. Sara was a lot better, but still nowhere near as good as Mom’s cooking.

The last week before we headed back home, Sara and I doubled down on our time together. She wanted to explore everything we could possibly do together, every sexual position we could come up with and anything else we could dream up.

“Sam, did you like anal?” Sara asked, her voice choppy and hesitant.

“What?” I asked, sunned Sara would even ask me something like that. “What do you mean, did I like anal? Why would you ask that?”

“What I mean is, do you want to try it with me?” Sara looked up at me with soft eyes.

It was obvious to me that she was worried, or something was up.

“Do you want to?” I answered with a question of my own.

“I think so,” Sara said but paused right afterwards. I saw her swallow as if she were fighting off a lump in her throat. “You took my virginity, and you were the first guy I gave a blowjob to.”

“So, what does that have to do with your ass?” I asked, still not understanding why she suddenly was asking me about anal sex.

“Nothing!” Sara snapped back. “I mean, everything I guess, but nothing.”

“That doesn’t make any sense, Sara,” I groaned. “Just tell me what you want.”

“I want you to put your dick in my ass, Sam. God!” Sara growled.

“Why though?” I questioned.

“Because ... I want you to be the first to do it. That way you were the first for everything...”

“Oh...” I suddenly felt bad about questioning Sara about the whole thing.

The two of us were quiet for a few minutes, just sitting there not daring to look at one another.

“Do you know how to do ... it?” I asked.

“Yeah, Amy showed me.”

“I thought you said no one had been in your ass!” I smirked, thinking I had just caught Sara in a lie.

“They haven’t!” Sara yelled. “I said, she showed me how to do it, not that she did it to me.”

“You did her—”

“Shut up, Sam. Right now.”

“But—”

“Sam, I mean it.” I knew from the look Sara was giving me that I was about to dig a hole deep enough to make it to China if I opened my mouth again.

“Sara, if you want to...”

“Yeah, tonight?”

“Umm, sure. Cool.”

That night, Sara was forceful in her need to get my dick inside of her. She started out by stroking me and then sucking my dick until it grew to full hardness. When she was satisfied, she quickly moved to straddle me and sank down on my cock. The feeling of her pussy was as wonderful as ever, but I was starting to wonder if she had changed her mind about me fucking her ass.

“I thought you wanted me in your butt?” I asked, both hands full of her tits as I watched her ride me.

“I do!” Sara answered, “Make me come first. Amy said that helps. It will be easier for me to take you there if I come.”

“Oh, cool.”

It didn’t take long for Sara to reach her first orgasm. I loved watching her come but what I wasn’t expecting was to come with her. She wasn’t expecting it either because her eyes went wide when she felt me twitch four or five times inside of her.

“Did you just come inside me?” Sara asked, her voice still shaky as her orgasm subsided.

“Yeah, sorry,” I answered. “I couldn’t help it. You felt so good, and I couldn’t tell you to stop because you were about to come too.”

“Okay, don’t pull out. You can usually get hard again pretty fast,” Sara said, her eyes locked on mine and there was a proud smile on her face. I had thrown a small wrench into her plans, but I think she was just as happy to know I couldn’t resist coming inside of her, which was true. “Do you want me to suck on your cock, or do you think you can get hard again faster if I keep riding you?”

As it turned out, she did both. She kept riding me for a while and then she lifted off me and started sucking my dick as if it were the most important thing in the world to her. It didn’t take long, and I was back to full rigidity.

“Ready?” Sara asked, her eyes sparkling because she wanted it now and was ready to go.

“Yeah, where do you want me?”

“Deep in my ass,” Sara grinned.

“You know what I mean,” I rolled my eyes but chuckled.

“Come on,” Sara said, getting off the bed, moving to the edge.

Sara put her hands on the mattress and bent over. She wiggled her but from side to side as if I needed encouragement. I laughed and moved into position behind her.

“Put it back in my pussy for a second first,” Sara instructed as she looked over her shoulder. I watched her eyes flutter as I drove back into her vagina hard enough that she had to catch herself before she fell onto the bed. “Mmm, fuck. Okay, okay. You gotta pull out or I won’t want you to.”

I pulled back, holding my cock in my hands as Sara widened her knees just a bit and arched her back dramatically.

“Okay, go slow and push it in.” Sara said.

I moved up and pressed the head of my dick against her ass hole and pushed.

“Ow, fuck!” Sara yelped before falling forward away from my cock. “You can’t just shove it in. You have to get it in the right spot and then gently push forward. Then I will push back against you too. Okay?”

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